Hydrazine → 6-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridine

HRID 590771Notes

Reaction equation

HRID 590771 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([CH3:10])[N:5]=[C:4]([Cl:11])[CH:3]=1.[NH2:12][NH2:13]>CC(N(C)C)=O.CCOC(C)=O>[Cl:11][C:4]1[N:5]=[C:6]([CH3:10])[C:7]2[CH:8]=[N:12][NH:13][C:2]=2[CH:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 1178709954,6-Dichloro-2-methylnicotinaldehyde

Product 1

HCID 1181689536-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4,6-dichloro-2-methylnicotinaldehyde (5.25 g, 23.48 mmol) in DMA (50 mL) was treated with hydrazine (7.37 mL, 235 mmol) at 0° C. The reaction was stirred for 15 min and then warmed to 80° C. for 2 h. The reaction was cooled and diluted with EtOAc and washed with water. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (0-100% EtOAc/hexanes) to give 6-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridine. MS ESI calc'd. for C7H6ClN3 [M+1]+ 168. found 168.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-612d03360f22425b81dde61fed4934ef
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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